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An Efficient and Green Synthesis of Highly Substituted N ‐Amino‐2‐oxo‐nicotinonitriles and Their Sulfonamide Derivatives under Ultrasonic and Microwave Irradiation
Author(s) -
ElSayed Hassan A.,
Assy Mohamed G.,
Mohamed Asaad S.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201903180
Subject(s) - sulfonamide , yield (engineering) , pyridine , chemistry , microwave irradiation , benzene , aryl , piperidine , catalysis , microwave , ultrasonic sensor , ketone , sulfonyl , nuclear chemistry , organic chemistry , materials science , alkyl , physics , quantum mechanics , acoustics , metallurgy
Abstract An efficient and facile approach has been described for the synthesis of a new series of 1‐amino‐2‐oxo‐nicotinonitriles and their sulfonamides under microwave and ultrasonic irradiation. The desired compounds 4 a‐l were obtained via condensation of p ‐chlorobenzaldehyde, aryl or heteroaryl methyl ketone and cyanoacetohydrazide in the presence of catalytic piperidine under three synthetic methodologies (namely, conventional method, ultrasonic and microwave irradiation), the best results (short reaction times, pure products, high yield) were obtained by ultrasonic irradiation. Sulfonamides 5 a‐f resulted via reaction of amines 4 a‐e and 4 j with benzene sulfonyl chloride in the presence of pyridine. The synthesized compounds give no significant results when investigated against Gm (+ve) and Gm (‐ve) bacteria, and fungi strains.